


Kiss of the Velvet Whip

by Niaxi



Category: Kim Possible (Cartoon)
Genre: BDSM, F/F, Latex, Strap-Ons
Language: English
Status: Completed
Published: 2021-01-01
Updated: 2021-01-01
Packaged: 2021-03-11 04:35:38
Rating: Explicit
Warnings: Graphic Depictions Of Violence, Rape/Non-Con
Chapters: 1
Words: 20,497
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28489173
Author URL: https://archiveofourown.org/users/Niaxi/pseuds/Niaxi
Summary: Kim Possible wakes up to find that she is in prison and must endure the torment and torture inflicted upon her by the cruel Captain Brooks; the warden of the facility. Dressed in a latex outfit, Kim must endure extreme punishment and sexual abuse at the hands of the dominatrix captain. Will she break and succumb to the Captain's will or will her iron will allow her to endure whatever torment is thrown her way? Warning: contains explicit content, non-consensual BDSM and rape.
Relationships: Kim Possible/Original Female Character(s)
Comments: 1
Kudos: 5





	Kiss of the Velvet Whip

**Author's Note:**

  * For [Celioxa](https://archiveofourown.org/users/Celioxa/gifts).



> WARNING! The following story contains graphic details of sexual acts, non-consensual BDSM and fetish play and rape. If you find any of these things upsetting or offensive then please stop reading now. 
> 
> For those of you who want to read on, I will briefly explain what you are about to read. This story was born from a discussion I had with a reader of my Kim Possible KimXShego story And You And I. In that story, Shego is inadvertently sent to jail by Kim and after discovering what happens to her rival while in prison, a guilty Kim breaks her out. Afterwards, Kim has recurring nightmares about being sent to prison for what she has done. This story is a non-cannon version of one of these nightmares, where she is subjected to punishment by the OC head of the prison facility; Captain Brooks. If you have not read And You And I don't worry about it, as I've already explained everything you need to know in order to enjoy this story. Also, just to make this crystal clear, Kim is twenty years old in this story. 
> 
> Finally, for those of you who don't know any of my fanfictions, I name my chapters after song titles and lyrics. In this instance, Kiss of the Velvet Whip is a song by Hawkwind and while the whip used in this story is not made of velvet, both the title and lyrics are fitting for this story. 
> 
> Enjoy.

There were three beds inside the threadbare cell; one on the left and right walls and another along the back wall. While it was not standard practice for the prison to allow more than two inmates to a cell, Captain Brooks, for her own amusement, had made an exception in this case and housed the three inmates inside a single cell inside cellblock C. The three women in question had been dubbed The Cellblock C Sirens and consisted of the supervillainess Shego, former cheerleader and high school bitch Bonnie Rockwaller and the latest addition to the facility, former world hero turned convict; Kim Possible.

Kim awoke with a start and her eyes darted around the drab, colourless grey walls. “What the…” she said under her breath, however, in the depths of her mind, she had the thought, _no… not again._ Her gaze quickly fell atop herself and the orange jumpsuit she wore. “Holy shit, I’m in jail!”

Scrambling to her feet, the hero took in the empty cots to her right and front and then the closed door of the cell. Without hesitating, she turned and made for the thick bars that stood between herself and the prison block and prayed that they were not locked. She needed to find someone; explain to them that there had been some sort of horrible mistake, that she; Kim Possible, did not belong in prison. However, before she reached them, a group of figures, appeared outside the cell, clad in blue shirts and black pants, except for the one in front; who wore a black shirt instead.

“Oh thank God,” Kim exclaimed at the sight of the guards. “There’s been some terrible mist…”

“Step away from the bars,” the harsh voice of the woman in the black shirt barked. Kim recognised the insignia on her uniform that marked her a lieutenant. 

“Please, you have to listen…”

“Step away from the bars, Inmate!”

The command was biting and Kim’s eyes caught sight of the taser on the woman’s hip and the hand now resting on it. _Shit, if I don’t comply, she’s going to use that thing on me!_ While the realisation shocked her, hesitantly, she complied and stepped back a few paces. In front of her, she heard the buzz of the electronic lock releasing and the bars slowly slid aside to allow four guards; all women, to enter the small cell.

“Please,” Kim immediately tried again, “I need to see the Captain, I don’t….”

“Oh, you’ll see the Captain alright,” the Lieutenant sneered.

“But I don’t know how much talking you’ll get to do,” a second added and Kim could hear an air of menace and amusement in their tone, which sent a shiver up her spine.

 _Whatever they’re here for, it's not to let me go._ Her eyes darted across the faces of the four women. _I’m going to have to fight my way out of here._

“Hold your wrists out in front of you and don’t move,” the Lieutenant then commanded.

 _Not going to happen!_ Kim immediately shifted herself into a guard, but before she even knew what was happening, the woman descended upon her. Kicking and screaming, they each grabbed one of her limbs and wrestled her to the ground. “No! Get off! Ahhh!” she yelled as she felt leg irons and handcuffs bite into her wrists and ankles respectively. Within moments, she felt the hands release her and she was left on the floor tugging at the thick shiny chain that joined her wrists to her ankles. “Fuck you! Let me go!” she spat; yanking on the chain with all her might, but it did not yield an inch.

“If you’re quite finished having a tantrum, then we had best get a move on,” the Lieutenant said, an air of amusement at Kim's plight lacing her tone. “Captain Brooks does not tolerate tardiness.”

Teeth ground, she made one last attempt to break the chain between her wrists but had no more luck than before. Two pairs of arms then reached down on either side and hauled her to her feet. Unable to do anything else, she allowed the guards to lead her out of the cell. _At least they’re taking me to see the Captain. Then I can straighten this whole mess out._

Inmates laughed and jeered at her as she passed them by, but none dared get to close to her and her entourage. Soon they had passed through the security doors that led out of the cellblock and were making their way through the complex and up to the top floor where she knew Captain Brooks’ office resided. However, instead of taking her through the door with the woman’s name on the glass, the guards led her further along the corridor to a heavy wooden one.

“Where are you…” Kim began but was swiftly cut off.

“Silence,” the Lieutenant barked and procured a key from the loop on her belt and inserted it into the lock. “We need to get you properly attired before you’re ready to meet the Captain.”

Kim automatically glanced down at her orange jumpsuit. “What do you mean properly attired?”

The door opened and she received a rough shove in the back by way of a response. The lights flickered on and she cast her gaze around the room. A large elegant wooden wardrobe dominated the right-hand wall, with a smaller matching chest of drawers beside it. A dresser, which clearly belonged to the same set as the other pieces of furniture sat directly in front of her and she could see her reflection in the large mirror that hung on the wall and spanned the unit’s entire length. Finally, on the left-hand wall, was a second mirror; this one full length and another door that she suspected led into the next room. Everything about the room she had just entered told her that it was some sort of dressing room and that knowledge immediately set her on edge.

Kim could feel the small hairs on the back of her neck stand on end as she was led across the deep red carpet and to the centre of the room. _What the hell is going on and what did she mean by attired?_ Above her head she caught sight of a thin metal bar dangling from a set of chains; it had a pair of leather cuffs at either end. _Fuck. What is that for?_

One of the guards must have seen her looking at it, as they said, “we only use that if an inmate is causing us trouble. However, you’re not going to cause us any trouble now, are you?”

The words almost felt like a challenge to Kim and she was about to spit, “I’m not cooperating with you,” in reply, when the Lieutenant turned to face her.

“She won’t cause us any trouble,” the woman’s blue eyes then pierced Kim’s olive-greens, “she’ll do exactly as she is told with no resistance, or she’ll go back to the hole for a **month**. Won’t you?”

Those words struck Kim like an ice-cold dagger to her gut and fear began to rapidly spread through her from the insertion point, as flashes of memory that she had been unaware of having stabbed at her mind. _Dark… no…pitch-black… and cold… so very cold… no light… no space… no way out…_ Kim felt her body tremble. She had faced so much in her life, escaped countless impossible situations and never been afraid. But the memory of being locked inside that tiny room in the pitch black and freezing cold brought about a feeling of dread so strong, that she knew the woman had been right; she would do whatever they ordered if it spared her a return to the hole.

Kim nodded reluctantly, “I’ll cooperate,” and immediately hated herself for it. _Damn it! I won’t give them the satisfaction of thinking they’ve gotten to me,_ so she quickly added, “so long as it gets me an audience with the Captain.”

The smile she received it reply unnerved her somewhat, but she did not let it show. One of the other guards then stepped forward and began unshackling her restraints. When the second leg iron was about to be removed, she gave half a thought to going on the offensive, but the memory of how easily overcome she had been back in her cell stayed her hand. _They were so fast I didn’t even see them move before they were atop me. No, I’ll bide my time until I can talk to the Captain. Hopefully, we can straighten out this mess and I can get out of here._

The guard who had removed her restraints stepped back and another immediately took her place. Before Kim knew what was happening, the woman had grabbed the zipper on the front of her jumpsuit and hauled it down. “Hey, what are you doing!” she exclaimed, but immediately caught the eye of the Lieutenant and immediately froze in the act of bringing her hands up to stop the woman, _…no resistance…_ Grudgingly, she lowered her hands back to her sides, just as the guard slipped the jumpsuit over her shoulders. It fell to the floor and bunched around her soft white shoes.

“Kick off your shoes and step out of your jumpsuit,” the guard who was undressing her commanded.

Biting back a retort, Kim did as commanded. No sooner had she removed her second foot from the bundle of orange, her white t-shirt was pulled up over her head, taking her arms with it. She heard it hit the floor with the lightest of noises before fingers expertly unhooked her bra in one go. The garment was pulled down her shoulders and she allowed her arms to move so the straps slipped down them effortlessly. Kim had to immediately fight the urge to cover her exposed breasts. _Don’t react, don’t give them the satisfaction. Just get through this and everything will be fine. You’ll sort everything out once you talk to the Captain._ Unfortunately, the desire to protect her modestly only ratcheted up tenfold when she felt the guard’s fingers slip inside the waistband of her white panties and haul them down her legs. When they reached her ankles, her socks too were removed.

Now completely butt naked, Kim met the gaze of the Lieutenant and could see the predatory look in the woman’s eyes, however, she did not turn away. _Why do I get the feeling that she’s checking me out?_ The second she had the thought, she felt her cheeks flush slightly, _dammit!_ She took a slow breath in through her nose to steady herself.

“Hold still,” a voice hissed in her ear and Kim almost jumped. So focused had she been on the Lieutenant that she had not heard the woman draw up behind her.

Next second, she felt hands gather together the strands of her long flaming-red hair and quickly tie it up in a high ponytail. The hands then reached around her shoulders and she just had enough time to see the black leather blindfold before it was placed over her eyes and plunged her world into darkness. “What the hell?” she exclaimed, as the strap was buckled tightly behind her head.

“Well, we wouldn’t want you to take any silly ideas into your head once you see your outfit now, would we?” the Lieutenant replied rhetorically. “Captain Brooks was most insistent that we avoid throwing you in solitary confinement at all costs.”

Kim felt anger begin to burn inside her and a strong desire to punch the woman, except that was completely out of the question now. Instead, she growled, “what outfit?”

“You’ll see,” the Lieutenant said, then laughed, “well, you won’t see, but you’ll certainly be able to feel it.”

Kim ground her teeth, _of course I’ll be able to feel it! How is that supposed to tell me what it is?_ From her right, she heard a sound that she knew must be one of the guards opening the wardrobe doors. _What the hell are they about to dress me in?_

Without warning, she heard the noise of an aerosol and felt a cold sensation, similar to mist spray, against her upper right thigh. The spray then moved quickly, covering her entire leg from that point downward. When it reached her ankle a voice commanded, “raise your foot and do not lower it until I tell you to.”

Knowing that she could not resist, Kim did as instructed and lifted her foot off the ground; perfectly balanced on her left leg. The spray quickly covered both dorsal and sole. She then heard a strange crinkling noise that sounded oddly rubbery and she was about to ask what on earth they were doing when she felt it. Against the tips of her toes, Kim could feel the cool touch of latex and it quickly spread over her entire foot and to her ankle. Like a second skin that felt slightly too tight, the material encased her foot and she motioned to pull it away, but a firm grip caught her ankle and pulled on it until it touched back down on the carpet. Next second, the latex stocking was expertly worked up her leg with little difficulty until it stopped midway up her thigh.

“Why are you dressing me in this?” Kim asked, unable to suppress the hint of worry in her tone.

“Because the Captain instructed us too,” the Lieutenant replied and Kim just knew the woman had an evil smirk on her face.

The entire process was then repeated on her left side, except for the fact she now knew what was happening and so lowered her own foot once the stocking had reached her ankle. A latex belt was then wrapped around her waist, fastened at the back with hooks and four suspenders clipped onto the tops of her stockings; two at the front and two at the back. When her foot was next raised, she felt something that she correctly deduced was some form of latex panties being slipped over it. After her second foot was through the undergarment, hands quickly pulled it up until Kim felt the cool rubber touch her groin and felt the one-inch waistband snuggly sit below her hips as the narrow material at the rear disappeared between her butt-cheeks. Her face turned red again at how tight, yet oddly not uncomfortable the material felt.

 _This will all be ok once I talk to the Captain… this will all be ok once I talk to the Captain,_ Kim desperately thought, however, a sinking feeling in her stomach was quickly telling her that none of this was ok, that something very untoward was about to happen to her. … _but I can’t go back to the hole…_ she practically cried internally, knowing she was resigned to allowing the guards to finish dressing her.

“Raise your arms out in front.”

On hearing the command, Kim obeyed and soon felt more latex against the soft flesh of her breasts, as the bra straps were worked onto her shoulders and the two halves of the backstrap hooked together.

“Which dress did the Captain request?” one of the guards then asked from the direction of the wardrobe.

“The black skater one with the red trim,” the Lieutenant answered.

The sound of clothes hangers being moved along a rail filled Kim’s ears for a moment before she felt her arms being raised into the air. She felt the cool rubber slip over her arms and touch her shoulders as the dress was worked over her head, the smell of rubber engulfing her nostrils. The hands of two of the guards worked it over her breasts and down her midriff until it sat snuggly on her shoulders and squeezed her lithe frame in just the right places. Even though she hated it on principle, hated the entire outfit, Kim was at least glad to have some degree of modesty back.

“Raise your right foot,” a voice commanded her once again.

 _What now?_ However, she complied nonetheless. Kim felt her foot being slipped into a pointed shoe and she could tell just from the slop of it that it had at least a six-inch heel. When it touched back down and the strap was securely buckled around her ankle, she felt a pair of hands steady her shoulders, as her other foot was lifted up and squeezed into the second shoe. It took Kim a moment to find her balance in such high heels when both feet were firmly planted on the carpet once more and the hands released her shoulders. She never wore shoes that she could not fight in and so capped the heel size at only three inches.

Kim then felt the same spray from earlier on her hands and wrists, before each was encased inside a latex glove. A clinking sound then reached her ears before two-inch wide metal shackles were placed around each of her ankles and wrists and locked with a padlock. A short chain; no more than five inches, was then placed between each set of cuffs. Then to her complete and utter horror, Kim felt a metal circlet placed around her neck and similarly locked. _They’ve put a fucking collar on me!_ Her humiliation only deepened when she heard the second click from the front that indicated that someone, probably the Lieutenant, had just attached a leash to it.

“What the hell do you think you’re doing!” Kim yelled and jerked her head back, only to find the leash quickly become taut. “Let me go and get me out of this damn outfit!” A chorus of laughter echoed all around Kim and her cheeks turned scarlet. “Fuck you!”

“I’d say she’s almost ready,” one of the guards then proclaimed.

“No, not quite,” the Lieutenant replied. “The Captain will want her face to look pretty. You know how much of a perfectionist she is.”

Kim then felt a tug on her leash, “this way, inmate.”

With her choices either being to comply or find herself flat on her face, she stepped forward and quickly found out just how short the chain between her ankle cuffs was. Stumbling, she just managed to keep her balance and had to take small steps in order to avoid tripping in her six-inch heels. When she felt her knees bump up against the dressers stool, one of the guards quickly spun her around and sat her down atop it. Then, much to her surprise, although in hindsight she should have anticipated it, the blindfold was unbuckled and removed. Light streamed into her eyes and even though it could only have been about fifteen to twenty minutes since it had been put on, she found it blinding and so promptly closed them again.

Like a doll, Kim sat as one of the women applied lipstick, blush, eyeliner and eyeshadow to her face. While her eyes slowly adjusted to the light, the guard spent so much time working on them that she could barely keep them open and even when she could, she could see nothing beyond the woman’s face, as she scrutinized her handiwork.

“There, perfect,” the woman then declared and stood up, taking Kim’s leash with her and so forcing her to stand. “Should I re-blindfold her?”

“Not just yet,” the Lieutenant replied and when Kim turned her head, she could see the smirk on her face. “I think she should get to take a nice look at herself in the mirror first.”

Against her will, she was led from the dresser and towards the full-length mirror. She almost closed her eyes, for she did not want to look at what she’d been transformed into. However, when the guard in front of her stood aside, she forced herself to stare at her reflection and her jaw hit the floor. She truly was a sight to behold. Starting at her feet, she wore pointed six-inch black heels with ankle straps that looked to have been shined to within an inch of their existence. But that was nothing when compared to the shine of her black latex stockings, the tops of which, along with the suspender belt and thong, which she could only assume were also black, were hidden beneath the skater skirt of her black latex dress. The dress hugged her figure perfectly and accentuated her breasts so that there was ample cleavage on display at the plunging v-neck, which had a thin red trim. A red latex belt, which she hadn’t even noticed the guards putting on her, encircled her waist where the dress body met the skater skirt. Her hands too were clad in black latex, up to about two inches above her wrists and had a flared red trim. Finally, she could see that the metal shackles were made of polished chrome and ‘popped’ against their shinny black backdrop. The collar was made of the same material and a chrome chair trailed off to where the guard who had done her makeup stood.

Kim met her own gaze in the mirror and could see that her lips had been coloured bright red and her cheeks blushed slightly, while black eyeliner and eyeshadow had been applied to her eyes. Finally, she managed to close her mouth. She looked nothing like herself, like the hero who had saved the world on countless occasions. Instead, she looked like a model out of some sort of fetish magazine. Despite how much it burned her to admit it, she looked hot… very hot. And had it not been for the severity of the situation and how she had been shanghaied into it, she might actually have liked the look. In fact, the slightly too tight feel of the latex felt strange but not in a bad way. However, the overriding feeling of dread for what was about to happen to her quickly retook control. _I **need** to talk to the Captain… make her understand that this is all just a mistake…_

“Ogling time’s over,” the Lieutenant then said sharply, causing Kim’s attention to return to the room.

Barely a few seconds after the woman had spoken, Kim felt the hands around her shoulders again and with one final glimpse of her latex-clad self, her world was returned to darkness. There was then a sharp tug on her leash and she was forced to once more take small steps in the direction that the guard led her. She then heard the sound of the second door opening and followed her leash holder through it. The moment her foot touched down, Kim could hear the sound of her heel on the floor and knew instantly that it was made of hardwood. A few steps later and the echo from her heels told her that the room must be fairly large, however, beyond that, she knew nothing.

Eventually, Kim felt the tension in her leash lessen and automatically stopped. _Urgh, this is exactly why I don’t wear such stupid shoes. Not only can I not fight in them, but I’ve only had them on for about ten minutes and already my feet are uncomfortable._ She heard the faint click from in front of her and knew the leash had just been unfastened from her collar, but the chrome circlet itself did not get removed, not that she had been expecting it to. There was then a second click from somewhere and all of a sudden, she felt her wrists being hoisted towards the ceiling as the sound of a metal chain being pulled rang in her ears. Only when her arms were at full stretch above her head did it stop.

“Another two notches,” the Lieutenant then commanded.

“No, please,” Kim said quickly, as her arms were already at their limit, however, she heard the clunking of the chain again and immediately her entire body tensed as the tension throughout it increased. “Ahh!”

“Now, be a good girl for the Captain, or you will definitely regret it,” the Lieutenant said, to which the other three women laughed.

She heard the women’s footsteps grow faint and then the sound of the door slamming closed. Now very much alone and very much afraid, Kim stood with her body stretched beyond its limit and dressed in a full black latex outfit like some fetish girl. _What on earth is the Captain planning on doing to me?_

##

How long Kim waited, with her arms slowly starting to ache and her feet becoming increasingly uncomfortable in her tight six-inch heels, she did not know. She’d futilely struggled against the steel cuffs and chain that held her wrists aloft and even stamped her foot in irritation when they had not given an inch. By the time she heard the first noise since the room door had been closed, the fear had ratcheted up and almost induced panic. It was a heavy click, perhaps more akin to a clunk, which finally reached her ears. The moment she heard the second one echo around the room and bring with it a menacing sense of foreboding, she knew that someone had just entered the room.

Kim turned her head in the direction of what she suspected were heeled boots crossing the hardwood floor. “Captain Brooks?” she called out, struggling to keep her voice level.

The reply sliced through the air and struck her like the crack of a whip, “silence!”

Whatever Kim had planned to say next was immediately driven from her mind. While she immediately recognised the voice as belonging to Captain Brooks, never had she heard it sound so dominant and forceful; an impressive feat for the domineering woman. And even she, Kim Possible; world hero, felt compelled to obey the command. The sound of the woman’s heels began to shift to her left and she turned her head to follow, but her neck quickly reached its limit. Snapping her head from side to side, she struggled to keep up with the Captain’s movements, as the woman circled her three times in ever-shrinking radius; like a shark closing in on its prey. The small hairs on the back of Kim’s neck once more stood on end when she realised what Brooks was doing, _she’s appraising me like I’m some pig at a farmers market!_ Her cheeks immediately began to burn and she felt a flash of anger cut through her fear, _I’m **not** some piece of livestock!_

“Yes, I think you’ll do nicely, Princess,” Captain Brooks then said, her tone light and almost with a lick of amusement; yet still very much dominating. And to Kim’s horror, the woman ran a latex clad finger lightly down her sternum and through her cleavage until it reached the neckline of her dress.

A cocktail of outrage and fear poured over Kim and she could not stop her body from jumping slightly upon feeling the touch of Brooks’ finger. And the idea of this hateful woman using Shego’s pet name for her, one that now warmed her heart and made her feel loved whenever she heard her lover say it, burned her to her core. Her reaction drew a cruel laugh of amusement from the Captain. “Please,” she began, a hint of desperation in her voice, “let me go, so we can sit and talk about this. I don’t belong here!”

“Be silent!” Captain Brooks barked.

A hand suddenly grabbed Kim’s chin and she struggled to shake it off, but the fingers pressed into her jaw and held her head in place.

“You are a deplorable criminal, who has been incarcerated in this facility so that you may be suitably punished for your crimes.”

As Brooks spoke, the woman turned Kim’s face from side to side and then released her grip on her chin. She then jumped when all of a sudden, she heard the Captain’s voice coming from behind her right ear.

“And given the nature of your particular crimes, I intend to carry out your punishment personally.” One second, the Captain’s voice was on her right, then the next hissing in Kim’s left ear, which caused her to visibly tense, “you are mine, Princess, and I am going to do whatever I desire to you. If it takes my fancy, I’ll take a cane to your backside and leave you with a bloodied cross centred on your asshole.”

Kim gulped upon hearing those words and knew that the woman spoke truly; she would do exactly that if that’s what she wished. The icy hand of fear slowly started to tighten its grip and any words of protest caught in her throat.

“Or perhaps I’ll flog your breasts until every scrap of skin is bright red,” Brooks continued.

A hand then caught Kim around the neck from behind and forced her head back. She jumped at the sudden feel of the Captain’s latex-clad fingers and a brief flash of terror shot through her when she felt the woman’s warm breath on her ear and for the briefest of moments, she could have sworn she felt lips graze it.

“Or if I’m feeling generous, perhaps I’ll straddle you over my padded leather bondage horse and fuck your pussy so hard with a thick black strapon that you’ll be screaming each and every time you orgasm.”

When those final words, spoken so close to her ear that it felt like she’d just heard a thunderclap, finally registered with Kim, sheer disbelief shattered through the fear and she exclaimed, “that’s rape! You can’t do that to me! It’s illegal.”

The cruel, high-pitched laugh that she received in response to her outburst sent a shiver down her Spine. “Do you honestly think anyone cares what happens to you now that you’ve been incarcerated here?”

Kim’s body tensed and she gasped loudly when she felt Brooks left arm wrap around her waist and the woman’s warm body press against her own from behind. The Captain’s hand then left her neck; a singular finger travelling down it and straight through her cleavage.

“You’re going to spend the rest of your life locked away here, where no one of any consequence will ever hear your story, Princess.”

As though to demonstrate her point, Brooks then snaked her left hand up Kim’s midriff. She almost exploded when the woman seized both of her breasts in a firm grip. “You can’t do that to me; any of it,” she yelled defiantly, her fear having now been replaced with fight. “I won’t let you! I swear, Brooks, if you so much as lay another finger on me, I’ll get out of this and... AHHH!” she moaned loudly as through her two layers of latex, Brooks found her nipples and squeezed both of them; sending an unwanted jolt of pleasure through her.

“I think that is more than enough out of you, Princess,” the Captain then declared.

Kim felt the woman’s right hand leave her nipple as the left twisted slightly, causing her to uncontrollably moan, “urgh,” and her mouth opened wide. “MMPH!” All of a sudden, she felt a hard silicon ball fill her mouth and a pair of leather straps bite into her cheeks as the black ballgag was buckled tightly behind her head. “MMPH!” Kim yelled again and stamped her right foot in infuriation at having been silenced by the gag. The ball was large and sat firmly behind her teeth, making it impossible for her to wriggle out of her mouth no matter how hard she tried. “MMPH!”

“Much better,” Captain Brooks then declared, amusement once more lacing her tone.

Kim then felt a latex clad hand give her right butt-cheek a hard spank; the blow stung, and her cheeks started to glow once more.

“I think after that outburst, you require some serious discipline, Princess.”

She heard the sound of Brook’s boots move away from her, followed by something being removed from a rack. When the woman returned, Kim felt her grip the back of her dress and the distinctive noise of the zipper being opened rang in her ears. She then felt the latex being slid down her shoulders as her back was fully exposed.

“My, those are some interesting scars on your left shoulder, Princess. Claw marks if I am not mistaken,” Brooks said in amusement. “A gift from your lover, I take it?”

Breathing slightly heavily through her gag, Kim growled at both the woman’s comment and the fact that her worst scars were currently being ogled.

“Why don’t we add some new ones?” Captain Brooks then said rhetorically. “Did you know that the cat o’ nine tails was most commonly used as the method of punishment in the British Royal Navy? So much so, that it was often referred to as the Captain’s daughter.”

The exact moment Brooks began to utter those final two words with force, a slight whipping sound accompanied them and the cat struck the site of Kim’s scars at the precise moment the final syllable was uttered. Biting down on her gag, she stifled a wince as the stinging sensation spread across her skin. _If she’s expecting me to cry or scream, she’s going to be disappointed._ _That was nothing compared to the pain I was in when Shego clawed my shoulder. I will **not** let her break me. _No sooner had she finished that thought, the second blow landed; this one across her right shoulder blade. Again, she felt the sting of the nine knotted leather chords on her skin but did not make a sound. She took a deep breath in through her nose and tried to focus all her attention on it. _Ahh,_ she hissed internally on feeling the third lashing; this one catching the lower left portion of her back. The fourth quickly followed on the opposite side, _ahh._

“You’re quite resilient, aren’t you?” Captain Brooks said, sounding almost pleased about this fact. “I think you are going to present me with an interesting challenge, Princess.”

Then, like lightning, Kim felt the sting of the cat strike her left then right shoulder blades; hitting the exact same spots as the first two blows. They came so fast and delivered so much pain, especially where a chord caught the sight of a previous lash that an audible wince escaped from behind her gag, “mmph.” _Dammit,_ she cursed internally on hearing it escape, knowing she’d just given the Captain her first small victory. _Savour it as that’s the..._ “mmph,” she winced again when the next two strikes caught sites three and four in quick succession.

Slap, slap, slap, slap! The sound of leather hitting skin echoed in her ears and caused her to see a series of bright red flashes behind her blindfold as the next round of blows landed on each of the four sections of her back so fast that the pain simply smeared from number one through to four with no way for her to distinguish from which blow any of it had originated. “Mmph!”

“I’m going to make you scream, Princess,” Captain Brooks hissed menacingly, “it’s only a matter of time. Perhaps if you surrender and do it sooner, I’ll be merciful and lessen your punishment.”

“Fuhh yuh!” Kim yelled in defiance but got the feeling that had been exactly the response the Captain had wanted to hear. Her muffled ‘you’ had barely left her mouth before, slap, slap, slap, slap! “MMPH!” Behind her blindfold, she screwed up her eyes as she struggled to focus on her breathing and take her mind away from the red-hot pain that now seeped into her from each of the multitude of thin red lines that covered her back. However, the sticky sensation that she felt from several of the wounds held her attention and she knew what it meant; Brooks had succeeded in drawing blood. _She’s going to pay for this. When I get..._

SLAP! The force of this singular blow eclipsed that of any that had preceded it and landed squarely upon her old claw scars. “MMPH!” Kim cried out, pain flooding her from nine new slices in the skin on her back. She struggled to choke back a tear. _I will not scream!_ SLAP! “MMPH!” Another set of cuts. SLAP! “MMPH!” SLAP! “MMPH!” Her breathing had become ragged and heavy through her mouth as she struggled to draw in enough air around the ball gag. Her back, now a canvas of thin red diagonal lines, many of which had blood trickling from them, felt as though it had been doused in petrol and set alight, such was the intensity of the agony that stabbed at her like hundreds of white-hot needles.

“Are you going to scream for me, Princess?”

SLAP!

“MMPH!”Kim cried and bit down harder on her gag. “Noh!”

SLAP!

“MMPH!” Her fingertips dug into the palm, but the effect was somewhat deadened by the latex gloves she wore.

“Are you going to scream for me, Princess?” Captain Brooks asked again.

SLAP!

“MMPH!” She took another ragged breath and felt a tear begin to form in the corner of her right eye. “FUH…”

SLAP!

“MMPH, MMPH, MMPH!” Kim cried, the pain having ratcheted up several notches after that latest round of strikes. “…YUH!”

SLAP, SLAP, SLAP, SLAP!

“MMPH! MMPH! MMPH! MMPH!” The cries came in such quick succession that they practically rolled into one another. Behind her blindfold, Kim finally lost control and felt hot tears begin to escape from her screwed-up eyes. The only saving grace being that the leather blindfold had been buckled so tight that it pressed up against her eyes and soaked up her sobs. On her back, she could feel the blood now freely trickling down in crooked lines from her multiple lacerations. _I… will… not… break…_

“I must say I’m quite impressed, Princess,” Captain Brooks commented almost lazily, as though she were peeling potatoes in the kitchen, not flogging another woman’s back to the point blood was seeping from the wounds. “You’re every bit as stubborn as I’d hoped.” The menacing edge, mixed with a twisted enthusiasm, then filled the Captain’s voice, “I think I’ll have to use a stronger method to discipline you.”

Kim remained defiantly silent, however, inside, she cried, _no… you can’t… I won’t…_ The tension in her over-stretched arms was suddenly released to the loud sound of the chain clunking through the pully. They dropped down and hung limp in front of her, but the lessening of the discomfort felt like only a small mercy in a torture chamber. She didn’t even notice when the chain was unclipped. Next second, she felt a hand grip the chain between her wrists and pull it downward. While she tried to resist, it was purely symbolic, for the flogging she had already endured had sapped her of a significant chunk of her strength. A pair of clicks signified a short chain had just been attached between her left-hand wrist and ankle cuffs. A third then accompanied the chain between her wrists being disconnected from the left cuff and quickly attached to her right ankle cuff. While she knew she could not straighten up, she tried anyway; another way of demonstrating her resolve to Brooks.

Kim felt the Captain seize the hem of her black latex dress and heard the sound of the rubber being bunched around her waist. The woman then pealed it forward towards her head and then worked it over her flaming-red ponytail and down her arms. The moment the latex parted company with her stomach, she became aware of the warm beads of sweat that clung to her midriff. However, it proved to only be a brief distraction from the searing pain in her back. With the dress now having left her arms, Kim felt the tension in the chain on her left-hand side vanish, however, it caught her too much by surprise that by the time she thought about trying to wrestle her hand free, it had been fed through the sleeve of her dress and reattached to her ankle cuff. Quickly, her brain told her that Brooks was about to do the same thing on the other side and so the moment she felt the tension release, she jerked her hand away as quickly as she could, only to have the Captain seize her wrist in a vice-like grip.

Captain Brooks tutted in response, “such disobedience. I suppose I’ll have to give you an extra punishment for that.”

Kim tried to shake her hand loose from the woman’s grip, but could barely shift it, as she heard the second arm of the dress being freed from the chain. A moment later and the tension in the metal links had returned. “Fuh yuh!” she spat into her gag.

“I’m afraid not,” Brooks laughed in evil amusement and lightly slapped a hand on Kim’s ass.

She let out a light gasp on feeling the soft strike on her naked flesh. However, Brooks did not remove her hand.

The Captain then began to grope her backside. “I’ll definitely be the one fucking you, Princess.”

A shiver ran along Kim’s bent and blood-covered spine. While the Captain had suggested that she might do that to her, this was the first confirmation she’d gotten that she planned to follow through with that idea. When she felt the icy grip of fear reach for her once more, she shook her head, _no… don’t think about that._ Except now that Brooks had put the notion into her head, she couldn’t not think about it. _Oh god! She’s going to rape me! Oh god, oh god, oh god!_ Unable to control herself, Kim began to hyperventilate. _No…. no… no…._ “NOH!” she yelled into her gag.

The Captain let out a shrill laugh, “don’t tell me the fearless Kimberly Ann Possible is afraid of a little black strapon?”

When Kim did not immediately respond, she heard Brooks chuckle to herself. She then let out a loud gasp when the woman’s fingers gently moved across her ass until they found her thong and followed the strip of latex until they came to rest on her vagina.

Brooks pressed her fingers lightly against her latex covered pussy as she said, “well, I say little, but I suspect you might find it to be quite filling, Princess.”

 _Oh god, oh god, oh god!_ As she struggled to get her breathing and heart rate under control, Kim heard the sound of the Captain’s heels clunk on the floor as the woman walked off in the direction of the rack she’d fetched the cat from. The only silver lining, if you could even call being told that you were going to be fucked by a woman wearing a black strapon a silver lining, was that it had temporarily distracted Kim from the pain in her back. … _she’s going to rape me…_

“While your ass is nowhere near as nice and round as your lovers, there’s still more than enough for me to work with, Princess,” Captain Brooks then said as she walked back towards Kim. “And you’ll find that I have impeccable aim.”

A swish and crack that could belong to nothing other than a whip, echoed around the room and caused Kim to tense. She’d struggled to withstand the cat and the ferocity the Captain had put into the last few sets of lashes from that, how on earth was she supposed to withstand a bullwhip? Kim’s heart sank, she already knew the answer to that; she wouldn’t. It was now simply a question of how much more pain could she withstand before she succumbed to Brooks’ desire and screamed.

Swish, crack!

“AHHH!” Kim cried as she bit down furiously into her ball gag on feeling the sheer intensity of the pain from the large red welt that had formed where the whip had struck.

“Scream for me, Princess,” Brooks commanded.

Swish, crack!

“AHHH!” she cried out again, the second stroke hitting the opposite butt-cheek this time. Her tears, which had subsided while Brooks had been removing her dress, returned with a vengeance and poured forth against the already damp leather of her blindfold.

“Scream, Princess,” Brooks ordered more forcefully this time.

Swish, crack!

It was only a combination of digging her fingers into her palms, screwing up her eyes as tight as possible and biting down as hard as she could on her ball gag that stopped her cry this time from becoming the scream that the Captain desired to rip from her, “AHHH!” The strike had hit the same mark as the first and Kim could feel the blood start to trickle from the laceration. _No... I... won’t..._

Swish, crack!

“MMMMMRGH!” the elongated cry tumbled out of her mouth as a searing pain tore through her; strike four having hit the same spot as strike two and ripped the skin open. Only vaguely aware of anything out with the agony that wracked her body, she heard the sound of the Captain’s heels approach her.

“You’re going to scream for me, Princess,” Brooks said with certainty, “and I think I want to hear it in full.”

Kim felt latex covered fingers in her hair and the bite of the leather straps against her cheeks quickly ebb, as the black ball dropped out of her mouth. The strap then came to rest on the back of her neck and the ball dangled a few inches from her throat like some fetish necklace. The Captain ran a finger across her burning cheek and she felt a tear that had escaped her blindfold being wiped away.

“Scream for me, Princess,” Brooks commanded. “Scream for me and I shall be merciful.”

At her command, Kim felt the urge to simply cave and do as the woman asked, to end her torment, or at least lessen it somewhat. Except her stubborn nature would not allow her to give in. She would break, of that she had no doubt. Only she could not bring herself to do so willingly. _If she wants me to scream, she’ll have to rip it from my body._ Taking in a laboured, but unobstructed breath, she uttered with as much steel as she could muster, “no.”

“You don’t disappoint, do you, Princess?” Brooks asked rhetorically, sounding pleased with this outcome. “I’m going to enjoy hearing your screams.”

After the sound of a few footsteps, Kim knew that the Captain had reassumed her position. _No..._ she wailed internally, knowing what was to come.

Swish, crack!

“AHHH!” Kim cried, through gritted teeth, sorely wishing she still had the ball gag to bite down on. _I... will... not..._

Swish, crack!

“AHHHH!” Tears poured freely from her eyes as the agony from the blows steadily mounted. _I... will..._

Swish, crack!

“AHHHH!” _I..._

The whip sliced through the air with a swishing sound that contained a slight whistle and the resultant crack as the tip flayed skin from flesh and left a bloody slash in its wake was almost deafening. However, this was nothing when compared to the sound that followed. Ripped from her body like the skin had just been from her flesh, Kim let out a pain-wracked scream, “ARGHHHHH!”

“That’s it, Princess, scream for me!” Captain Brooks commanded forcefully.

SWISH, CRACK!

“ARGHHHHH!” she screamed again, the agony bursting through her like water through a hole in a dam.

“Scream for me!”

SWISH, CRACK!

“ARGHHHHH!”

“SCREAM FOR ME!” Captain Brooks bellowed, a deep-seated anger at something Kim could not possibly comprehend fuelling her sadistic desires.

SWISH, CRACK! SWISH, CRACK! SWISH, CRACK! SWISH, CRACK! SWISH CRACK!

Her world consumed by a hot blood-red colour, Kim knew nothing except for searing agony as the strikes rained down on her and her screams became a continual torrent of her anguish. When finally the last blow struck and no more followed it, the jagged spikes in the blanket of pain subsided and left her with a constant searing sting across her entire backside, eclipsing and overriding any pain she may still have felt from her back had the skin on her ass not just been flayed. Her breaths came in laboured pants and her heart raced faster than Ron running from danger. Her body quivered uncontrollably and it was perhaps a miracle or a testament to her inner strength that she remained upright.

“Doesn’t that feel so much better, Princess?” Captain Brooks asked, her voice almost soothing, like she had just shown Kim a great kindness. “To know that you have been punished for your crimes?”

Kim heard the Captain’s voice through the wall of pain and knew two things: first, Brooks expected an answer and two, if she gave the wrong one, the hateful woman would pick up the bullwhip again... or something worse. However, it was still somewhat grudgingly that she replied in a haggard voice, “yes.”

“That’s a good princess,” Brooks replied and to Kim’s horror, the woman patted her on the head like she would a dog. “I think you deserve a reward for that. You’ll find that, while I will punish you severally for your crimes and transgressions, if you behave and do as I instruct, I am a fair Mistress and as such will reward good behaviour.”

Kim was left with her humiliation and to wonder what exactly the woman had meant by that. While the pain no longer held the same excruciating barbs it had while she was being whipped, it still washed over her like a balm laced with ghost chilli peppers, stabbing at her across each of the rends in her flesh.

The sound of something being placed on the floor between her legs drew her attention and next second, she felt a large, hard spherical object press her black latex thong into her crotch. “What are you doing?” she gasped in alarm. She shuffled her feet forward away from the object, only to feel agony spike in her backside, as two latex covered hands spanked both her butt-cheeks. “AHHHH!”

“Hold still, or I’ll get my whip back out,” Captain Brooks commanded in a no-nonsense tone.

The mere threat of the woman fetching the bullwhip was enough to freeze Kim in place and she quickly felt the spherical object press firmly into her crotch once more. “What is that?” she asked in alarm, however, did not dare move.

“It’s called a magic wand, Princess. And you are about to find out exactly what sort of magic it can do.”

In truth, she had not needed to hear the answer. While she was unfamiliar with the toy in question, she was not so much of a novice that she did not know exactly what it would do. “Please...” Kim begged, “...don’t do this to me.”

“What? After you were such a good girl and screamed so beautifully for me?” Captain Brooks replied in mock offence at her unwillingness to enjoy the toy. The woman then laughed, “in a few minutes, you’ll be begging me not to stop.”

“No, I... ahhh!” she cried out upon suddenly feeling the wand start to vibrate. The ripples passed through her latex thong and spread out over her entire vaginal area. Against her will, Kim felt a small jolt of pleasure cut through the pain and her cheeks turned crimson. “Please... you can’t... ahhh!” a second jolt, like a small spark of electricity shot through her as the Captain increased the speed of the vibrator.

“It sounds like you’re going to enjoy this reward, Princess,” Captain Brooks said in amusement. “However, if you want to cum, you’re going to have to work for it.”

“Ahhh!” she groaned, unable to stop the unwanted feelings of pleasure and desire slowly begin to stir inside her from beneath the blanket of pain. The sound of a something being moved across the floor then reached her ears, but other than that, she had no idea what was going on out with the blood-drenched cocktail of pleasure and pain that was being shaken up inside her. Kim then felt the Captain’s latex-clad fingers on her back and the hooks on her bra being undone. A moment later and the black latex fell away from her small breasts and dropped to the floor with a rubbery flop. A pair of firm hands then seized her breast and began to knead them like they were balls of dough. “Urgh!” she moaned on feeling unwanted pleasure ripple through her.

“Does that feel nice, Princess?” Brooks asked in response to her moans.

While the Captain’s grip was firm, it did not cause pain and when combined with the constant vibrations against her clit, the blood-red mist that had engulfed Kim’s mind throughout the whipping started to turn a shade of pink, as the pleasure continued to swirl through the pain. “URGH!” Kim moaned loudly, the only reply she could give. _No... I don’t... want... this..._ “UHHH!” she cried in delight as Brooks pinched both of her nipples and began to lightly twist them, “UHHH!”

“Aww, doesn’t that just feel so good, Princess?” Captain Brooks said in a condescending tone.

Kim felt the intensity of the vibrations increase at the exact same time as her tormentor’s fingers lightly upped the pressure on her nipples and it sent a shockwave of pleasure through her. “AHHH!” she exclaimed in delight, which immediately sickened her. _No... I... don’t... want... this..._ “AHHH!”

“Do you want me to make you cum?” Brooks then asked, her dominating tone having returned.

“No...” she managed to utter through a panted breath, only for the intensity of the vibrations to shoot up and for the Captain to increase the speed of her finger work on her nipples. Pleasure coursed through Kim’s body, almost masking the pain entirely and she could not stop the string of moans from escaping her mouth and calling her a liar.

“I think you’re lying to me, Princess,” Brooks said, her tone conveying a stark warning, _‘you don’t lie to me.’_ “Do you want me to make you cum?”

The word no immediately formed in her mind, but through the continual moans of delight, the word, “yes,” slipped out of her mouth in a shaky voice and Kim hated herself for it and hated her body for betraying her so.

The intensity of the vibrations suddenly dropped and the Captain released her nipples, however, what stimulation remained on her clit was still more than enough to keep her on edge and send small jolts of pleasure through her. Hands then reached behind her head and she felt the buckle of her blindfold being removed. The leather mask came away from her face and she had to close her still tear-stained eyes as the light assaulted them. A few moments passed in which she was allowed to let them adjust before she managed to fully open them. And the sight before her made her gasp.

“Do you see this?” Captain Brooks asked firmly.

Kim took in the view of black latex covered thighs and stomach, which framed the open zipper of what she assumed was a catsuit and the shaved vagina that sat mere inches from her face. She nodded in response.

“Have you ever eaten pussy before, Princess?”

Kim didn't answer, still far too stunned at the sight of the woman's shaved vagina sitting barely six-inches from her face. _Surely she isn’t expecting me to..._ “ARGH!” she half cried, half screamed when the Captain stuck both cheeks of her ass with her latex-clad hands.

“Have you ever eaten that green bitch’s pussy, Princess?” Brooks demanded, her voice loud and imposing.

Out of fear of having her lacerated backside struck again, Kim quickly nodded. _Oh god! She expects me to pleasure her!_ She’d only ever done this with Shego and the thought of performing a sexual act on someone other than her lover felt abhorrent. Only she knew she had little choice. Brooks had already proved more than capable of making her scream and would undoubtedly not hesitate to do so again if she refused the command. And she knew she could not withstand that level of agony again.

“You’re going to eat my pussy until I cum, Princess. Do you understand?”

Kim raised her head slightly, her gaze travelling over the Captain’s shiny black latex waist cincher, up the front of her catsuit, past a pair of thin lips that wore immaculately applied dark red lipstick and to a pair of merciless grey eyes. As always, Brooks’ dark brown hair had been tied back in a pristine high knot. Even though Kim knew the woman must be forty, her perfect features did little to telegraph it. And everything about the woman’s appearance compelled her to nod in submission. Trepidly, she lowered her gaze back to the woman’s shaved vagina and her mouth towards it. However, still two inches away, she felt a hand grab the back of her head.

“To slow, Princess,” Brooks barked.

Unable to do anything to stop the Captain, Kim’s head was thrust forward and her mouth and nose buried into the woman’s crotch. “MMPH!” she yelped, her voice severely muffled by the soft flesh that now surrounded her mouth.

“Lick it!” Captain Brooks yelled at her in a voice that left no room for debate.

However, Kim struggled to comply, for to do so would feel like a betrayal of Shego and the intimate moments they had shared. Only when she tried to take a breath, she realised that she could barely inhale any air. She tried a few more breaths, let out another muffled, “mmph!” and tried to pull her head out of the Captain’s crotch so that she could get some much-needed air.

“Lick it and I’ll let you breathe.”

Kim heard Brooks’ words, struggled for a few more seconds and tried to take in one last frantic breath, all the while her brain telling her that she had only two options; suffocate or lick. Grudgingly, she chose the latter, _Shego… I’m sorry._ Opening her mouth, she stuck out her trembling tongue and slid it between the Captain’s labia.

“That’s it, Princess, now lick it.”

Still short of air, Kim slowly started to lick up and down Brook’s warm and soaking vaginal area. _Why is she so wet, this is the first sexual thing she’s done, isn’t it?_ While she had been blindfolded for the bulk of the encounter and the woman could easily have had some sort of toy pleasuring her before she unzipped her catsuit, she just knew that had not been the case. _She got this wet… got such a sexual thrill out of making me cry and scream in agony! What sort of person is she?_ She felt the hand on the back of her head relax its grip and Kim gratefully pulled it back so she could gulp down some much-needed air. He olive-green eyes then found Brooks’ clit and she knew she would not get away with the meagre licks she’d given thus far. With no other choice, she lowered her mouth back to the woman’s vagina, _…I’m so, so sorry, Shego._

The tip of Kim’s tongue found the swollen nub that was the Captains clit and she began to delicately lick under the hood. _The sooner I make her come, the sooner I can stop._ In slow, steady circles, she ran her tongue around the other woman’s clit. A few low moans reached her ears and made for a moment made her feel as though she had the situation under control. Only for Brooks to remind her of who was boss.

“Faster!” the Captain barked and Kim suddenly felt the woman’s hand seize the back of her head again.

Face once more pressed into Brooks’ crotch, she had no choice but to pick up the pace. Like it was a vibrator, Kim flicked her tongue from side to side, then up and down and then around in circles. Shego had taught her exactly how to please another woman and she’d had plenty of practice. Only never before had it felt abhorrent to hear the individual, she was pleasuring moan in delight.

“Get your tongue inside me!” Brooks then commanded sharply and increased the pressure on Kim’s head.

While she quickly stopped flicking the woman’s clit and lowered her tongue, it was not quick enough for the Captain’s liking.

“Get it inside me!”

Pain shot through Kim’s left butt-cheek as a latex clad hand spanked her, the sharp smack noise quickly followed by a muffled cry. However, she had to push the pain from her mind and force herself to quickly comply with her tormentor’s latest instruction, or risk suffering further anguish. Reaching the Captain’s opening, she slipped her tongue inside the warm lips of the woman’s vagina. The pressure on the back of her head increased again and so she involuntarily delved deeper.

“Find my g-spot, Princess,” Brooks barked as she let out a long moan.

Kim had done this exercise with Shego before and had found the tip of her tongue could only just reach that of her lovers. _What if I can’t find it?_ She had to suppress a wave of panic at that thought and found the roof of the Captain’s vagina with the tip of her tongue. Slowly she slid it forward, searching for the rough patch and praying that she could find it. When she’d gone as far as she could go, she was forced to open her mouth and practically take the woman’s entire vaginal area inside in order for her tongue to search even further in. The pain quickly returned and she was about to go into a full-on meltdown over what the Captain might do to her when finally she felt the rough patch of flesh above the tip of her tongue and heard Brooks let out a loud moan. Pre-empting the instruction, Kim slid her tongue back and forth over the woman’s g-spot, eliciting further moans.

“Faster, Princess,” Captain Brooks ordered through a series of moans, but her tone did not quite have the same hard edge as before; the pleasure clearly softening her ever so slightly.

Kim complied and shot her tongue in and out as quickly as she could, however, she was quickly running out of air. Desperate to make the woman come; to finish the horrible act, she ignored the warnings and kept going. The Captain’s moans intensified in tandem with her running out of air. _Come on you…_ faster and faster her tongue flicked over the woman’s g-spot, as her lips began to suck around Brooks’ entire vaginal area; applying pressure on her clit.

“URGH!” Brooks yelled, as both her hands grabbed Kim’s head and forced it as deep as possible into her crotch.

Now desperately in need of air, Kim’s body began to shake in her bonds, as her heart rate increased and a series of heavily muffled cries escaped from her mouth. Only when she thought she might pass out from lack of oxygen did she finally feel the Captain’s grip relent, allowing her to pull her head back. Coughing, spluttering and with cum dripping from her lips, she swallowed mouthfuls of air until she managed to regain some measure of control over her breathing.

“I see that green-skinned bitch you fornicate with has taught you some measure of skill, Princess,” Captain Brooks said, barely sounding impressed. “However, I have much higher standards than she clearly does, so I will be expecting you to improve greatly.”

While she heard the words, Kim was still too busy regulating her breathing to understand the Captain’s meaning. Suddenly, the intensity in the vibrations coming from the magic wand, which was still positioned directly against her own latex-clad clit, shot up and her mouth opened wide as a loud, “UHHH!” escaped from between her lips. She then felt the woman’s fingers begin to lightly pinch at her nipples, eliciting a smaller moan with each touch. As the seconds ticked by with her suspended in this heightened state of pleasure, Kim felt the need to cum quickly begin to build inside her once more. Brooks firm hands then began to massage her breasts, stoking the flames of desire and delivering increasingly close waves of pleasure. “UHHH!”

“That’s a good girl,” Brooks said mockingly. “Do you want to cum?”

The vibrations increased again and Kim felt a wave of embarrassment, shame and guilt wash over her as she cried out, “yessss! UHHHHHH!”

“Ask permission and I’ll let you cum,” the Captain instructed, her words almost challenging Kim to do so without first asking.

Mortified at the very suggestion, she forced herself to grit her teeth and tried to suppress the pleasure. _I will not ask her permission to…_ “AHHHH!” she cried out in delight, as she felt both nipples being pinched at the same time and twisted.

“As permission and I’ll let you cum.”

 _I will not…_ “uhhh, uhhh, uhhh, uhhh!” Kim panted in quick succession, She could feel her orgasm building and knew that if the Captain continued along her present course, she would cum regardless and bring the woman’s wrath down upon her. Hating herself for how Brooks was making her feel and for betraying Shego, she managed to utter through a series of moans, “please… may… I… cum.”

“What was that, Princess?” Brooks yelled at her.

Kim knew full well that the Captain had heard her, knew that the woman simply wanted to humiliate her further and despite how much she hated her for it, the sheer pleasure that was coursing through her body had left little room for any thought other than one, _I **need** to cum! _And so, through her moans, she cried out, “please may I cum!”

“I can’t hear you, Princess!”

“PLEASE MAY I CUM!”

“CUM, PRINCESS!” Brooks yelled at her.

Kim felt the vibrations shoot up and her eyes rolled into the back of her head as a sea of ever-changing colours swirled around her and brought a powerful orgasm crashing down atop her, “URGHHHHHHHH!” All of her muscles tensed and she drowned in a torrent of bliss that felt both incredible and tainted by something evil at the same time. When the pleasure eventually subsided and she could see straight once more, Kim felt dirtier than she’d ever done in her entire life. She’d just allowed a woman who was not Shego to forcibly orgasm her and begged her for the privilege no less. _How could I have let her do this to me?_

“Did that feel good, Princess?” Captain Brooks asked, her tone one of mocking amusement.

“Fuck… you…” Kim uttered through a panted breath. _I will not submit to you!_

In front of her, she watched Brooks calmly rise from the padded black leather and chrome recliner she had been sat on and re-zip the crotch of her latex catsuit. “Well, that is an unfortunate attitude for you to have. I suppose you require some further discipline in order to help you understand your position, Princess.”

 _Shit, what is she going to do to me now?_ With no blindfold on, Kim could now see the thigh-high black boots, with six-inch heels that had been tormenting her so much with the menacing sound they’d been making on the hardwood floor. However, soon her head had craned as far as it could go without her falling over and so she was again left to wonder what exactly Brooks intended to do to her now.

After a few anxious moments, the Captain finally spoke, “you’ll learn that not all discipline and training involves floggers and whips.” The sound of those six-inch heels then drew closer once more. “You’re going to learn to be receptive to pleasure when you are allowed it, Princess.”

Brooks came back into view, sat something down atop her chair and then turned to face her, a chrome bar, about one-and-a-half-feet long, in her hands. Kim watched the woman as she attached a clip in the centre of the bar to her collar and then let it dangle from it. The captain then bent down, unclipped the chain that held her left wrist to the respective ankle. She struggled futilely, a lot of her normal strength having already been sapped, as Brooks bent her arm towards the collar and fastened the cuff to the end of the bar. Even though she knew she could not win, Kim still put up a show of resistance as the process was repeated with her right wrist. Once she had been properly re-restrained, Captain Brooks took hold of the bar and tugged on it until she once more stood upright.

“What is that for?” Kim said in alarm on seeing her tormentor picking up what looked like a large clear plastic wine glass but without the stem.

“You’re about to find out, Princess,” Brooks replied with a sneer and placed the plastic cup over Kim’s left breast.

“What th… ahhhh!” she half moaned; half cried when the pressure on her small breast suddenly increased and it began to expand inside the cup. A glance at Brooks had revealed a small device with a hand-trigger was attached to the cup. She watched the woman squeeze it again and let out a second moan-cry as her breast continued to expand. “What is th…ATTT!” It took two more pulls of the trigger, each followed by a more painful cry for her breast to fill the cup; the pressure on it having ratcheted up.

“These are suction cups, Princess,” Brooks said as she removed the pump, fetched a second cup and placed it over Kim’s right breast. “And they are going to do a very nice job of increasing the sensitivity of your breasts.”

She let out a series of moan-cries as she helplessly watched the Captain repeat the process on her other breast.

“And it will also do the exact same for your clitoris.”

Kim’s eyes widened in horror when she saw the smaller cup in the woman’s hands. Instinctively, she tried to shuffle backwards, but the Captain easily caught her by the waistband of her latex thong. Next second and the piece of clothing had been hauled down to her ankles.

“Well, look at you, Princess. You are positively soaking,” Brooks said with a high-pitched laugh.

For the umpteenth time, Kim’s cheeks burned scarlet and she felt another cocktail of embarrassment, shame and humiliation get poured over her, only this time she could add a sense of betrayal to the mixture. By letting Brooks do this to her, she had betrayed Shego. _How can I possibly face her after what I’ve done?_ “URGH!” Kim moaned loudly, as she felt the small suction cup get placed over her clitoris and labia and pumped once. “URGH, MMPH, ARGH!” she exclaimed in quick succession upon feeling the pleasure turn to pain with each subsequent squeeze of the trigger.

“In a few minutes, all your fun places will be nice and extra sensitive,” Brooks said upon removing the pump. “Now, stay here and don’t move a muscle. If you lose even one of those cups, I’ll cane the backs of your legs, do you understand?”

Kim felt the icy hand of fear reach out for her again on hearing the punishment should she manage to shake one of the suction cups loose. So, instead of turning to keep an eye on what the woman was heading off to fetch now, she remained still as a statue and waited. True to the Captain’s word, it was a few minutes before she heard the sound of heels draw up behind her once more. The woman’s latex-clad hands then came around Kim’s chest from behind and took hold of the suction cups.

“Are you ready for the pain, Princess?” Brooks whispered in her ear.

Kim’s spine stiffened at the sound of the Captain’s voice and the content of her words made her tense. “Wait, please don… AHHHH!” she cried out, as Brooks ripped the suction cups off of her breasts; instantly decreasing the pressure. The entirety of her boobs ached as they hung limp; both them and her nipples still temporarily enlarged.

“We’re not finished yet, Princess,” Captain Brooks then said and Kim could picture an evil smirk on the woman’s face.

She took a deep breath and tried in vain to take her mind away from what she knew was about to happen. “AHHH!” Kim cried again, as she felt the suction cup that had been on her vaginal area being ripped off. Her clitoris quickly began to throb and felt like it was pulsating. She then felt the Captain wrap a wide leather belt around her waist and buckle it tightly. “What’s that for?” she asked; looking down at it. Between her legs, she could see a pair of short leather straps dangling, with a third threaded through them parallel to the belt.

“For holding this, Princess,” the Captain replied, as she stepped around to face Kim; the magic wand in her hand.

The woman then bent down and buckled the powerful vibrator to the belt and then adjusted the straps so that the hard rubber head of the device pressed firmly against her clit. A small jolt shot through her when it made contact and Kim suddenly became aware of just how sensitive she now was down there, if only temporarily. However, that brief jolt was nothing compared to what she experienced a moment later when Brooks switched on the vibrator. “UHHHH!” Kim moaned loudly and felt her body quiver from the sensation. _Oh god, she’ll be able to orgasm me so easily while I’m like this._ She let out an elongated groan of pleasure and resignation when the speed of the vibrations increased.

“Cum without asking permission and I’ll cane the backs of your legs,” Brooks then said firmly, simply swapping out the crime from her last declaration of punishment method for this new one.

While the sensation was not yet great enough to make her come, she knew that it would be all to easy for her tormentor to turn up the vibrator and force her over the edge. Meaning she again had no choice; she’d either have to endure another round of agonising punishment, which she had neither the physical or mental strength for, or do as the Captain had instructed and ask for permission before she orgasmed. “I hate you!” Kim half yelled; half cried in frustration.

“I don’t particularly care,” Captain Brooks sneered. “I’m going to make you submit to me one way or the other.”

She grit her teeth in response and to stifle another moan. “I won’t submit to you!”

The Captain let out a high-pitched laugh and picked up a small metal box. “You will, Princess, don’t worry about that. While you might still be trying to delude yourself, I can tell that you are already halfway there. Your will has been eroded, as evidenced by the fact that you’ve already asked my permission to cum once already. Now it is only a matter of time.”

Kim watched as Brooks removed what looked like a small silver clamp with rubber tips from the box. _Shit, I’ve got a bad idea I know what…_ “ahhh!” she cried out when she felt the clamp bite down hard on her right nipple. “Ahhh!” the second one bit into her left nipple with a similar ferocity. The speed of the vibrations then intensified slightly, causing her to let out a third moan, this time of pleasure, “uhhh!” The Captain quickly added a second pair of clamps to the flesh of her breasts, resulting in a stronger cry of pain. Yet again the speed of the vibrations was increased and this time Kim found herself struggling to stay in control as a string of groans escaped from her lips.

“Do you want to cum, Princess?” Brooks asked leisurely, most certainly already knowing the answer.

 _No…_ “yes…” she cried out, again immediately hating herself for both admitting it and feeling that way in the first place.

“Then ask for permission and you can cum.”

Kim almost broke down into tears at how wretched the situation made her feel. Everything she allowed this hateful woman to do to her felt like a dagger in Shego’s back that had come from her own hand. Yet she knew she could neither fight her body and the desire she felt to cum nor survive being canned, which left her with the despicable choice of doing as the Captain had instructed. “Please may I come?” she finally wailed.

The vibrations increased at the exact same time as Brooks said firmly, “cum, Princess.”

Kim came. Like someone had put a rocket up her ass, she was blasted through cloud nine and into orbit. Tainted pleasure cascaded over her and made she felt a twisted combination of ecstasy and abhorrence. When she came down enough to think straight, her immediate thought was a dual, _urgh… so good… more_ and _Shego… I’m… sorry…_ “Uhhh,” she moaned and to both her horror and elation, she realised that Brooks had not turned the vibrator back down. 

“Enjoy the pleasure, Princess?” Brooks asked rhetorically, for it would have been obvious to any observer that Kim had. “Now it’s time for the pain. You don’t get pleasure without pain.”

She struggled to raise her head to meet the Captain’s gaze, as the woman fished inside her metal box for some more clamps. “AHHH!” she cried out upon feeling the next pair bite into the flesh of her breasts. Another pair quickly followed, “AHHH!” Both sets were far tighter than the previous ones had been. The hot, stinging pain from her breasts threatened to engulf Kim’s mind, just like that from when she’d been whipped and flogged, but the constant jolts of pleasure refused to yield. Then Captain Brooks turned up the vibrator again. “URGH!” Kim moaned as a pleasure wave crashed over her and another orgasm began to build. Uncontrollably, her hips began to buck slightly as she tried to force the device further into her pussy.

The Captain let out a high-pitched laugh. “I think you’re beginning to enjoy yourself, Princess. Would you like some more?”

Kim again found herself torn between what her body craved and what her mind knew she should do. Agony smeared all over her now sweaty face, she nodded her head.

“Ok, but remember, you can’t have the pleasure without the pain,” Captain Brooks replied and plucked another two clamps out of her box.

“ARGH!” she screamed on feeling the viciously tight clamps bite into her flesh. Again, the red sea of pain clashed with the swirling technicolour of pleasure and came so close to overcoming it that Kim almost broke down into a flood of tears, except the Captain chose that moment to increase the speed of the vibrator. “UHHH!” she cried out, pleasure now fighting back hard. As the pair fought for control, she felt another orgasm begin to build. “Uhhh, uhhh, uhhh,” she moaned in quick succession, the fires of desire now starting to eclipse those of the agony. “Please…” Kim began, knowing that she was powerless to stop the orgasm from hitting, “I need… uhhh… permission to… UHHH… cum… UHHHHH!” _OH GOD, I’M NOT GOING TO BE ABLE TO HOLD IT…_

A latex clad finger reached out and tilted her chin upwards until her olive-green eyes met the merciless greys of Captain Brooks; a thin smile on the woman’s face. “You may cum, Princess.”

“URGHHHHHHHHH!” Kim screamed in ecstasy as the floodgates opened once more and tainted pleasure crashed down atop her. Legs already quivering and feet more than a little uncomfortable from having been stuck in the six-inch heels for so long, she would have fallen over had it not been for the intervention of the Captain, who caught her around the waist and held her upright.

“Careful, Princess, I wouldn’t want you unintentionally damaged,” Captain Brooks said, her words conveying a dark sense of irony. Slowly, the woman lowered Kim to the floor. “You must really enjoy being a submissive little bitch if you can get off like that while enduring such high levels of pain.”

Kim shook her head in disgust, but only succeeded in drawing a cruel laugh from her tormentor. _I don’t enjoy this… I can’t enjoy this…_

“You enjoy this, Princess,” Brooks declared emphatically. The woman then turned the vibrator up to what surely must have been its maximum. “Don’t you?”

Kim felt her body begin to convulse as wave upon wave of pleasure crashed over her. “No… I… URGH!!!” she cried out, her voice a twisted mix of disgust and delight.

“Admit it and you can cum,” Brooks yelled at her.

“No…” she wailed, elongating the word as tears began to pour from her eyes, “I…”

“Admit it and you can cum!”

“URGHHHH!” Her hips began to violently buck against the vibrator, she could feel the orgasm coming and she wanted nothing more than to revel in the ecstasy it would bring.

“ADMIT IT AND YOU CAN CUM!”

“YES!” Kim screamed as the most powerful orgasm she’d had yet exploded inside her and caused every single muscle in her body to convulse. Eyes closed; body and mind completely drenched in pleasure, she did not notice nor care that the vibrations had stopped and that the Captain was busy removing the clamps from her breasts. The vibrator was removed next, followed by the cuffs around her ankles and her shoes. Even when Brooks latex clad body pressed up against her own to release her wrists and remove the chrome bar from her collar, she barely batted an eyelid.

Kim finally came back to her senses when she heard the sound of her latex stockings being peeled off her legs. However, she offered up no resistance as the Captain rolled her over and removed the collar from around her neck. Now completely naked, she simply lay there, utterly drained, as the sound of her tormentor’s heels on the floor travelled away from her. She did not know how long it took for the sound to move back towards her, simply that she had not moved in that time. While she still felt the pain from the lacerations in her back and ass, the sheer level of pleasure and the lingering euphoria had been enough to deaden a large chunk of it. _What’s happening to me?_

Like a ragdoll, Kim offered up no resistance as she felt Captain Brooks bend her lower left leg up towards her backside and then start to coil a double-columned rope around her ankle and upper thigh; it was black. She felt a slight discomfort when it was pulled and knotted tight, but did nothing to try and fight the woman off. A second rope was then added closer to her knee. The Captain then repeated the process with her right leg until Kim’s was in a perfect frog-tie. She then felt strong hands grip her shoulders as she was pulled upright. Her head swayed and the room spun slightly at the sudden motion and it took her a few moments to properly stabilise herself. In that time, more rope was coiled around her upper forearms and then around her torso; above and below her breasts, with another pair of double-columned strands running from the centre of her back, up over her shoulders and then down and around one breast respectively. Finally, her wrists were brought together behind the centre of her back and lashed together with rope that was connected to the coils that wrapped around her torso. Only when the Captain had finished and she felt the woman stand up, did it properly register with Kim that she had just willingly allowed herself to be tied up. _What is happ…_

“Do you see this, Princess?” Captain Brooks asked firmly as she stepped in front of her.

Kim stared, eyes once more wide and fearful and nodded. For it was impossible for her to miss the long, thick black strapon that protruded from the Captain’s crotch.

“Good girl. Now, you’re going to open your mouth and start worshipping it. Do you understand?”

The terror of what this meant, of the fact they were rapidly approaching the endgame, held her in its icy grip and so she shook her head, _no… I… can’t… I… won’t…_

“No?” Brooks mocked, “then I’ll make this one quite simple for you, either you open that pretty little mouth of yours and suck my cock,” the woman’s voice then quickly turned into a yell, “or I shove it up your tight little ass hole with no lube whatsoever!”

The fear hammered into her by the Captain’s voice shattered that Kim had felt from the first sight of the strapon and she quickly found herself nodding. The woman then put a hand around the back of her head and moved the head of the black dick up to her lips. Trembling, her lips parted slowly and she stuck out her tongue and touched it against the rubber tip.

“Lick it, Princess,” Captain Brooks commanded sharply.

Kim obeyed and began running her tongue all over the head of the strap. She’d never done this before, not with Ron nor with Shego; just another thing for her to add to the bucket of firsts Brooks had imposed upon her that night. Hesitantly, she began to circle around the head, not really sure what her tormentor expected from her, just knowing that she would quickly find out if she did it wrong.

“Don’t just stick to the head, Princess, there’s an entire ten-inches for you to worship.”

Taking it as an order, she began to run her tongue along the length of the strapon, feeling the thick rubber veins that ran from the base of the tip all the way down the shaft to the stem. _There’s no way this is going to…_ out of fear, Kim had to force that thought out of her mind, _…don’t think about… that…_ Having worked her way around as much of the Captain’s cock as she could, she felt the woman pull her head back to the tip.

“Now suck it, Princess. Suck your Mistress’ hard dick.”

Her lips parted once more and the already wet strapon slipped between them and into her mouth. Slowly Kim began to bob her head back and forth on the tip, not daring to move further down the shaft for fear of choking. Only it quickly transpired that was non-negotiable and she cried out around the head of the cock when she felt the Captain seize her ponytail.

“Suck it, Princess!” Brooks yelled at her and mercilessly shoved Kim’s head forward towards her crotch.

Gagging and spluttering around the thick black strap, she could do nothing to stop it forcing its way down her throat. Her body began to shake as she struggled to breathe and only when she thought she could take it no longer, was the cock hauled out of her mouth. Gasping for air, a line of spit dangled from the tip of the dick and arced back to her bottom lip. “Please…” was all she managed to splutter before the Captain forced her head forward again and she did not even have time to think about closing her mouth before it was once more violated by the merciless strapon, which forced itself even further down her throat this time. “MMPH, MMPH, MMPH!” Kim cried around the cock, as she again started to run out of air and she desperately began to shake in her bonds, only for Brooks to hold her firm. Her eyes had almost rolled into the back of her head when she once more found herself coughing and spluttering.

“I’ll make a cock-sucking slave out of you yet, Princess,” Brooks then proclaimed and let out a cruel chuckle.

“Please… no… MMPH!” before she could even finish her plea, the strapon had been shoved back inside her mouth. Only this time her tormentor pulled it back and forth in quick succession.

“Look at me, Princess!” the Captain commanded. “I want to see those pretty little olive-greens of yours while I face-fuck you.”

Afraid of what might happen if she refused, she raised her gaze to meet with those unrelenting grey eyes and saw the thin, twisted smile on the woman’s face. And again, Kim found herself wondering just what sort of person could get off on being so vicious and horrible to another person.

“I think my cock should be well lubed by now, Princess,” Captain Brooks then said upon finally removing the black strap from her mouth.

Still struggling to properly breathe, Kim was only aware of what was happening when she felt the ropes running up and over her shoulders bite into her flesh; the woman had grabbed hold of them and picked her up off the floor with on hand. Dangling a foot above the ground and utterly helpless, she was carried a short distance across the room and set down atop a grey rug that felt like rabbit fur. Balanced on her knees, the Captain then lowered her face down onto the soft rug but kept her lacerated ass in the air; one hand maintaining a hold on the ropes. Kim then felt the familiar touch of the magic wand press itself against her clit, she hadn’t even noticed the woman picking it up. Terror then shot through her when she felt the slippery tip of the strapon press itself against the opening to her vagina.

“I’m going to fuck you until you submit to your new mistress and confess your crimes, Princess,” Captain Brooks then said matter-of-factly.

Absolutely terrified, Kim fought with what little strength she had left to desperately try and get away from this hateful woman, from what she knew was about to happen to her and from the tiny part of her that craved to submit, to call the woman mistress and enjoy the pleasure she knew would be forced upon her. She thrashed from side to side, but with only one hand, Captain Brooks effortlessly held her in position. In sheer desperation, she screamed, “NO, PLEASE… I’M STILL A VIRGIN!”

The high-pitched, mocking laugh that followed rang in Kim’s ears and she did not need to hear Brooks horrible words to know that the woman would enjoy every second of her torment. “I know, Princess, however, that should be virgin past-tense.”

Then it happened. With one hard thrust, Kim felt the black strapon drive inside her, taking her womanhood and sending a red-hot pain, like her vagina had been set aflame, shooting through her. She screamed. Loud and long, she screamed, half at the pain; half at the horror of the situation, as the Captain began to fuck her. In and out the woman’s dick thrust, each stroke penetrating deeper than the last and sending a mini-shockwave through her. “ARGH! PLEASE, STOP,” Kim screamed in agony, “I DON’T WANT THIS!”

The only response she received was to feel the sensation of the magic wand begin to vibrate against her clit and like with the nipple and breast clamps before, she felt the pleasure begin to duel with the pain, only this time the latter had already begun to recede. “No…” she wailed when the first proper wave of tainted pleasure hit, realising that this was far worse than simply being in pain, “…please… stop.”

“Since you’ve been such a good girl thus far, Princess, on this one occasion, I’m going to allow you the privilege of orgasming as many times as you like without having to ask my permission,” Captain Brooks replied, her tone laced with amusement.

For a brief moment, Kim could not understand why her tormentor, who had threatened her with such severe punishment should she cum without permission earlier, would freely allow her to do so now, especially for such a paper-thin and phoney reason. However, as the woman continued to thrust into her and her first orgasm began to build, she realised that Brooks had just robbed her of the last form of resistance she had left. They both knew she would orgasm sooner or later and the Captain had just removed the only choice she had; to take punishment over willingly asking for permission.

Tears began to pour from Kim’s eyes when the first orgasm hit and even though she cried, “I hate you!” her body betrayed her and convulsed in pleasure with an, _‘I love this.’_

“That’s it, Princess, cum for your new mistress,” Brooks said in amusement but did not relent with her thrusting. “Now are you going to submit to me? Are you going to submit to your new mistress?”

“No!” she cried in defiance of her body, two thick wet lines now running down her cheeks.

The fucking and vibrations against her clit ceased and Kim was momentarily left motionless on her knees; the Captain’s grip on the ropes that snaked their way over her shoulders and around her breasts the only thing keeping her sweaty and anguish riddled face from hitting the floor. “AHHH!” she cried when suddenly, Brooks grabbed her ponytail in her free hand and then let go of the ropes with her other. Now being held up by her hair, a sharp pain, although nothing like what she had already endured, shot through her scalp, as she felt the black strapon move back towards her opening. “Please… no… AHHH!” she cried in pain as the rubber cock slammed into her once more.

The sound of Brook’s latex-clad hips slapping against Kim’s sticky red ass was accompanied by a cry of pain with every instance of contact, as they continuously hit parts of her four bloodied lacerations. “Please… stop… AHH!” she wailed in anguish, although at present the agony was once again higher than the pleasure. At least until the Captain turned the magic wand back on. “MMMH!” she cried as the vibrations shot through her still hyper-sensitive clitoris and sent a fresh wave of pleasure to join that she was already receiving from the strapon and fight against the pain in her backside.

Harder and deeper the Captain pounded her pussy, all the while the vibrations against her clit steadily increasing. Her swollen breasts bobbed back and forth and even though her tormentor had used soft rope, still chaffed slightly against their bondage. However, this slight discomfort went virtually unnoticed against the backdrop of what was happening at her rear. Even though her pain receptors still fired each and every time Brooks’ hips slapped against her ass, the pleasure from the strapon penetrating deep inside her and rubbing furiously over her g-spot, coupled with that the magic wand relentlessly delivered to her clit, had become enough to override it.

“URGH!” Kim moaned, as the intensity of the vibrations shot up and her tormentor increased the ferocity of her fucking. It only took a moment or two at this new pace for Kim’s second orgasm to be ripped from her by the Captain’s black cock and it was accompanied by a shriek that was a tortured mix of pleasure and emotional anguish; the physical pain having now been eclipsed.

“Are you going to submit to your new mistress, Princess?” Brooks barked loudly.

“Urgh!” she groaned as the relentless wave of pleasure continued to tear through her without resistance, however, she somehow managed to still cry out, “no.”

The thrusting stopped again, with the strapon once more slipping out of her opening and quickly the vibrations died. Panting, Kim tried in vain to regulate her breathing and could feel her heart beating a million miles per hour. _I… can’t… keep… going… like… this…_ She then felt the Captain’s free hand take hold of her left breast, the tension in her hair vanished and soon the woman was holding her above the rug by both of her swollen boobs. Dangling above the rug, she could do nothing to stop Brooks from pulling her upright. Her aching vagina rested atop the shaft of the strapon and she felt the warm latex of the woman’s catsuit press up against her lacerated and bloody back and ass. She winced in pain, but it quickly transitioned into a moan when Brooks began to knead her tits. Like her clit, both boobs and nipples were still extra sensitive and so even such light finger work was enough to set the pleasure cycle in motion once more. And then the Captain pinched her nipples, “UHHH!”

“Does that feel nice, Princess?” Brooks asked airily.

Kim moaned again and while she desperately wanted to say no, to reject the tainted pleasure that had started to flow through her again, her body had already betrayed the truth to Brooks and she no longer had the strength to face the punishment for lying. “Yes,” Kim grunted reluctantly through another moan; the Captain having begun to lightly twist her nipples.

“That’s a good princess,” Captain Brooks whispered softly in her right ear, her left hand reaching up and gently stroking Kim’s cheek. “Are you going to submit to your new mistress?”

While Kim’s torn mind wrestled between her feelings of revulsion and rejection of the pleasure she’d been subjected to and her uncontrollable and unwanted desire to receive more of it, she felt the Captain’s left hand leave her cheek and snake its way down her body to her soaking pussy. “UHHH,” she moaned upon feeling latex-clad fingers start to pinch at her still swollen clit.

“Are you going to submit to your new mistress, Princess?” Brooks asked again, the forefingers and thumbs on both hands rapidly pinching nipple and clitoris respectively.

“URGH,” Kim cried out, pleasure jolts shooting through her from both sites and making her wish that her tormentor had another two hands, so that her second nipple and her g-spot could also receive such skilled attention. She immediately hated herself for having that thought and in her disgust, she spat, “no!” It was the wrong answer and she knew it, now she would have to suffer the consequences.

“So, be it, Princess,” the Captain replied, her tone conveying a hint of sadistic delight, rather than irritation at the fact she’d just been defied. It seemed that even in defiance, Kim lost; the woman wanted this to drag out for as long as possible.

She received a sharp pinch that morphed into an agonising twist to both her clit and right nipple, which forced a cry of pain from her. Brooks then leaned her forward slightly and Kim felt the woman’s latex covered chest press harder against her back, eliciting further cries from her, as pain once more spiked in the bloodied lashes on her back. Her tormentor’s left hand then left her clit and when she lowered her gaze, she could see it now holding the strapon. “Please… not again,” she wailed but could do nothing to stop the black cock from finding her opening once more and driving into her so hard that it hit her cervix. “URGH!” Kim grunted, half in pain; half in pleasure on feeling the impact and it came as a surprise that the dick did not spew out of her mouth. She tried to brace herself for the thrusting to begin, but it never did. Instead, she felt the magic wand being pushed against her pussy, only this time it was the side that touched her clit, while the head pressed firmly up against the small segment of the strapon shaft that was not buried inside her. Suddenly, the vibrations then shot up from zero to one hundred.

“UHHHHH!” Kim yelled in delight, the vibrations not only shooting through her clit, but passing along the strapon shaft and so reaching every scrap of her vaginal walls; including her g-spot. Brooks left hand then returned to her breast. In the space between her thumb and forefinger, the woman gripped her nipples, leaving the rest of her fingers free to knead her breasts. It seemed the Captain had just given her exactly what she had wanted; every one of her erogenous zones being stimulated at the same time. Body shaking under the ministrations of her tormentor, Kim struggled to in vain to fight the tainted pleasure and soon found herself drowning in an unwanted desire for more… for the stimulation to increase… for the orgasm that she felt rapidly building from deep inside her. “URGHHHHH!” she screamed, her body having now completely surrendered itself to the ecstasy. The Captain, seemingly knowing that she was close to climaxing, squeezed both breasts and nipples hard; while simultaneously thrusting her hips and pulling Kim’s body into the strapon. The black cock pressed deeper inside her; the wand more firmly against its shaft and her clit. Pleasure exploded through her like a firework had just been set off inside her body and Kim felt all of her muscles contract, however, was most aware of her vaginal walls tightening so much around the strapon on that had she been capable of thought, she would have expected it to crumple.

Only when her body finally unclenched itself, did she feel the vibrations stop. The Captains grip on her breasts lessened and the woman gently allowed her to flop down atop the grey rabbit fur rug. Heart still racing, Kim could not control her panted and ragged breaths. Her vagina ached again and she was acutely aware of the strapon slipping out of it again and drops of a sticky liquid trickle down her thighs. _…sweat…_ she could only muster that one thought, _…please let it just be sweat…_

Kim felt Captain Brooks latex-clad fingers run up the inside of her right thigh. “My, my, Princess, it seemed that last orgasm caused you to ejaculate.”

 _Oh god… no…_ She felt her cheeks begin to burn in humiliation, having not even known she was capable of ejaculating. She’d wanted all her firsts to happen with Shego… all her firsts should have happened with Shego. Yet here was Captain Brooks taking so many of those from her lover and it was becoming increasingly difficult for Kim to reject the woman’s skilful touch… to reject the tainted pleasure the coursed so freely through her.

“Now then, Princess, are you going to submit to your new mistress?”

Once again, the question reached Kim’s ears and her mind immediately went to war with itself over how she should answer. And even the part of her that wanted it all to end, did not know if that meant she should fight or submit. She knew what the Captain intended to do if she continued to fight, but what might the woman do if she submitted? Her mind then travelled to her lover. _Shego… I’m so, so sorry… I’ve betrayed you._ Unfortunately, that didn’t help. For no matter what she did, the outcome would only be a further betrayal of the woman she loved.

“Well?” Captain Brooks demanded in a vicious bark, “are you going to submit to your new mistress, Princess?”

“I… I… I c…c…can’t,” Kim wailed, tears now forming in her eyes.

“Then I’ll just have to make you,” Brooks answered determinedly and ran her fingers, the same ones as before, up Kim’s left thigh.

In front of her face, she then saw the shinny latex of her tormentor’s hand and the sticky juices that had come from her own pussy that covered them.

“Your cum has made a mess of my gloves, Princess. So, you’re going to clean them,” Captain Brooks ordered, and then barked at her, “lick my fingers.”

She did not respond, simply stared at the woman’s shinny fingers and the cum that glistened on them in the rooms soft yellow lighting. Her hesitation did not go down well and she immediately felt the Captain’s other hand grab her right breast, find the nipple and twist it harshly. “AHHH… MMPH!” Kim’s cry of pain was quickly muffled as latex-clad fingers were roughly shoved into her mouth.

“Suck your slave juices from my glove, Princess!” Brooks yelled at her. “Or I’ll take a cane to the backs of your thighs!”

The threat of the punishment was enough to shatter Kim’s resolve and so she slowly began to rub her tongue along each of her tormentor’s long, pointed fingers as she sucked; ensuring she got each and every drop of her slightly sweet with a twist of salt cum, like warm honey that had dribbled off of a hunk of gammon. Just to be sure she’d done the job properly; Brooks ran her fingers around her mouth and forced her to gag before removing them.

“Next time you won’t hesitate, Princess,” Captain Brooks then declared with certainty. “Now, after such disobedience and your refusal to submit, I think you need a little more pain to teach you who your mistress is.”

“Please… no…” Kim cried as she was helplessly pulled up from the rug by the ropes that snaked over her shoulders and under her breasts by the hand she’d just been forced to clean. “AHHH,” she yelped on feeling the bite of the rubber covered metal clamp when it bit into her right nipple.

“These are clover clamps,” Brooks explained.

Kim felt a metal chain run across her back and down her other side. This was quickly followed by the cruel bite of a second clamp on her left nipple, “AHHH!”

“And they should do a good job of teaching you who your mistress is, Princess.”

Tears now ran down her cheeks and she knew they were not simply a result of this latest dose of pain she was receiving; her resistance had almost been completely eroded and it would not be long before she submitted to Captain Brooks demand that she call her mistress. Kim once more felt the tip of the merciless black strapon against the opening of her vagina and hated herself for the desire she felt to have it inside her once more; to feel it thrust deeper and deeper as the Captain fucked her. “Ahhh!” she cried out when suddenly Brooks pressed her face into the rabbit fur rug and the strapon entered her once more. The head of the magic wand was then refocused on her clit and the vibrations turned on. Kim felt the pleasure slowly begin to ripple through her at the same time as her tormentor began to fuck her. The first moan of delight was ripped from her within seconds but quickly followed by a yelp of pain, Brooks having grabbed the chain that connected the clover clamps and started to tug on it.

Spikes of pain began to penetrate the continual wave of pleasure as Brooks’ hips once more slapped against her lacerated ass. A hard thrust from the strapon again hit her cervix and added another barb of pain, but it quickly vanished into the backdrop of pleasure that still coursed through her from the magic wand. She felt the strapon slowly withdraw, only for it to be rammed inside her again with the same level of force.

“Are you going to submit to your new mistress, Princess?” Brooks yelled at her again, the woman continuing this new rhythm of singular deep thrusts that punctured the pleasure with brief spikes of pain; each one accompanied by a sharp tug on the clover clamp chain.

“…no…” Kim wailed and she could feel her resolve begin to weaken, “…oh god… UHHHHHH!” she screamed as another orgasm hit. Only she had little time to revel in the aftermath as she felt the vibrations increase in speed yet again. “AHHH! Please… stop!” she cried in anguish, the pleasure having turned to discomfort as her clit was over-stimulated. Had Brooks deliberately chosen to spoil her orgasm? It did not take her long to reach an answer; yes, her tormentor had. Everything the woman had done since entering the room had been deliberate and designed to break her. “Please… no more.”

Slowly Kim felt the strapon begin to move and gently rub over her g-spot. “Uhhhh,” she cried when the discomfort in her clit finally receded and the pleasure began to flow again. On hearing her moan, the Captain quickly ratcheted back up to a relentless pace. In-out, hard and fast, Kim felt her hips begin to involuntarily buck against the hard black cock; anything she could do to increase the pleasure. She could no longer deny it, her body wanted this too much. “UHHHHH!” the next orgasm hit her so fast and like a tonne of bricks, she was surprised she hadn’t exploded into a thousand ecstasy-soaked pieces.

“Submit to your new mistress, Princess!” Brooks screamed at her; hand pressing harder against Kim’s face and burying it into the soft rabbit fur.

Strapon and vibrator ceased their movements as her body slowly slid back down the pleasure mountain. Gasping for breath, she struggled not to inhale the fur of the rug and could not even muster enough ait to reply. Then, her tormentor seemingly knowing exactly when her body was ready to receive stimulation again, Captain Brooks switched the magic wand up to maximum and began to hammer the strapon into Kim’s pussy once more. Less than a minute later, she felt another orgasm being ripped from her body. And this time the pleasure was too much; she could no longer resist. She belonged to Captain Brooks and would allow the woman to do anything to her if it meant she’d be allowed to experience such bliss again.

“Are you going to submit to your new mistress, Princess?”

“YES!” Kim screamed through the torrent of tainted pleasure, tears now pouring from her eyes.

“YES, WHAT?” Captain Brooks yelled at her, tugging sharply on the clover clamp chain.

“YES, MISTRESS!”

“Good girl.”

Kim’s body hung limp as Captain Brooks moved her hand from her head and once more seized the ropes that ran over her shoulders and around her breasts. Her eyes had rolled into the back of her head and a small dribble of drool clung to her bottom lip. And when the pleasure from her last orgasm finally ebbed, her only thought was to experience it again. Seeming able to read her mind, her new mistress dutifully complied. The fucking of her pussy and vibrating of her clit started again and like a rag doll, Kim’s hips bucked against the strapon and her breasts bounced in delight. She no longer cared that submitting was a betrayal of all she stood for and of her lover, she just needed to feel the pleasure cascade over her. To drown in the ecstasy of lust and desire that her mistress’ cock gave to her. And that’s exactly what she got. Kim’s tired and tortured body clenched when one final orgasm was ripped from it, only this time there was not a hint of the taint that had stained all the previous ones, simply the divine bliss that came from being fucked by her mistress.

“You like being fucked by your mistress, don’t you, Princess?”

When she did not immediately answer, Kim felt her pussy being harshly pounded until she screamed, “YES, MISTRESS!” Only then was the black strapon finally fully withdrawn from her. Body unbelievably weak, with sweat covering every inch of her skin, she was pulled upright and held there by her mistress; who clutched the ropes draped over her shoulders in a single latex-clad hand.

“Do you want another taste of your cum, Princess?” Captain Brooks asked, almost making it sound like a genuine question.

Kim knew that only one answer would please her mistress and she put up no resistance to giving it, “yes, Mistress.” When the Captain came into view, she could see streaks of red on the front of her shiny black catsuit… streaks of her own blood. However, the moment the black strapon was presented to her, she did not hesitate to open her mouth and start to lick the tip. Pressing her lips to her mistress’ cock, Kim began to suck it of her own accord, bobbing her head forward and back, taking it as far into her mouth as she could without gagging, then forcing herself to deepthroat it, all in the name of pleasing her mistress.

All of a sudden, she felt her mistress shove her shoulders and she fell backwards. Hitting the floor; her bound wrists and arms cushioning her fall, Kim felt the air being knocked out of her. Next second, Captain Brooks was descending upon her.

“It’s time for you to confess to your crimes, Princess,” her mistress said and Kim could see the stern expression on the woman’s face.

She felt the strapon press against the opening to her vagina and a hand seize the two double columns of rope that ran through her cleavage. “Yes, Mistress,” she shrieked the second the woman’s dick thrust into her once more. The veins along the shaft began to rub at her g-spot as her mistress began to furiously fuck her once more.

“Then let’s get started, Princess. Did you fraternise with a known supervillain?”

“Yes, Mistress,” Kim cried out, upon feeling the cleansing power of the black strapon pound at her. “URGH!

“Did you allow a supervillainess to escape from justice?” Captain Brooks yelled.

“Yes, Mistress,” she replied again, pleasure coursing through her like fire and burning the corruption that her crimes had inflicted upon her soul from her. “MHHHHH!

“Did you aid a supervillainess in escaping from jail, Princess?”

“Yes, Mistress!” The speed of Captain Brooks strokes increased and Kim knew her mistress intended to make her cum as she confessed her most heinous of her crimes. “AGRH!” she cried and felt the orgasm about to be torn from her body, ripping out the last of her secret sins.

“Did you or did you not have romantic relations with a known supervillainess, Princess?”

“YES, MISTRESS, I DID!” Kim screamed as she felt her orgasm about to explode inside her.

“AND WHO WAS THIS SUPERVILLAINESS, PRINCESS?” Captain Brooks bellowed at her.

Kim could not contain herself and she screamed, “SHEGO!” as the ecstasy coursed through her, the orgasm driving the last of her crimes into the light.

When she could finally see through the ever-changing colours that clouded her vision, Kim’s olive-green gaze met with one from her mistress’ merciless greys. “You’ve committed several serious crimes, Princess. However, do not despair, your mistress will ensure you receive the punishment that you deserve for each and every one of your actions. Won’t that make you feel better, Princess?”

Kim could see in her mistress’ gaze that the woman meant every word, that she would suffer untold agony as she paid for each of her crimes until the red had been completely expunged from her ledger and instead drawn from her own flesh. And if that was the cost of being made to feel so good, she knew she would willingly pay it. “Yes, Mistress,” she replied obediently, “I need you to help me pay for my crimes.”

“Good girl, Princess,” her mistress praised and withdrew her strapon from inside Kim. “And if you are very good, I might have your little playmate brought here for you to play with,” there was a brief pause as a vicious smirk formed on her mistress’ dark red lips, “under my careful supervision of course. Now, I have a gift for you, Princess. Something that will serve as a constant reminder of to whom you now belong.”

“Mistress?” Kim asked in confusion, as she watched the woman stand up and walk towards a long wooden table with multiple implements spread out across its surface; her heels clunking on the floor. When her mistress returned, she could see what looked like a pair of titanium earrings and a thin needle in her open right palm and a box of alcohol wipes clutched in her left hand. The woman then pulled her up onto her knees.

“Now, hold still, Princess, this is going to hurt, but if you squirm, you’re liable to tear your nipples,” her mistress said firmly.

Although Kim quickly realised what the woman was about to do, she knew that she could not resist. She’d committed so many crimes and needed to be punished for them and if her mistress decided that this was something she needed to endure; she would comply without complaint. She then felt the cool touch and mild sting of an alcohol wipe clean and sterilize her right nipple. Taking a deep breath, she screwed up her eyes and waited. The sharp sensation of the needle piercing her flesh and hollowing out a section of her nipple caused pain to once more shoot through Kim, however, in comparison to what she had felt earlier in the evening when her ass had been getting whipped, it was not unbearable. Within seconds, she felt the needle pass out the other side, the ring being inserted and heard the faint click of it closing. The process was then repeated on her left nipple, with the hot pain again lasting only moments but not comparable to that from earlier. When she opened her eyes, Kim looked down and saw the pair of shiny titanium rings; each with a small ball at its base, hanging down from her erect nipples, a few drops of blood still clinging to the edges of the puncture sites. Each a symbol that she would continually feel against her skin, a reminder that she now belonged to her mistress.

“You did well, Princess,” her mistress then said, almost sounding pleased with her. “Now, I’m going to have you cleaned and returned to your cell. I hope when you reflect on tonight you remember that this is what you deserve and that you are going to be perfectly obedient from now on.”

Kim nodded, “yes, Mistress.” She then felt the tension in her bonds being released and soon after the ropes were removed from around her arms and torso; the four around her legs quickly following. Collapsing into a sweaty and completely drained puddle on the rabbit-skin rug, she listened to the sound of her mistress’ footsteps get further away. Her body had slowly started to cool when she finally heard the sound of a door opening and closing; signalling that the hateful woman had now gone. Kim let out a low breath as she struggled to raise her head. That had been intense, torturous and unfortunately, pleasurable beyond imagination. She felt her nipples sting slightly when she looked down at the rings that now hung from them. She’d lost the battle, there was absolutely no question about that. However, the rings in her nipples were a symbol that she faced a long, hard war in front of her.

 _Captain Brooks wanted me to break… and she got what she wanted… I caved… I submitted… I called her mistress… But I’m not beaten. She may break me down and force me to submit to her will over and over, but I will never truly be hers._ Her fists clenched in a sign of resistance as she sat up. _Somehow, someway, I’m going to get out of here with Shego and then we can be together._ Her gaze then slowly cast itself around the large room and she gasped at what she saw. On one wall was a large rack that contained at least a dozen different whips, canes, floggers and paddles. Beside that sat the long wooden table, displaying countless different types of leather and metal restraints; many of which Kim could not name. There was also a chest of drawers beside it, which she just knew was full of neatly arranged toys of some variety. Her eyes then passed over a machine that had a long, thin chrome pole sticking out of it with what looked like a rubber dildo on the end. She did not want to think about what that might do. Further around, she saw what looked like a tall gymnastics horse, which also had what looked like a pair of dildos affixed to its surface. In the next corner sat a longer horse, covered in black leather and with padded rails along each side on which legs and arms could be rested and restrained. To Kim, it looked as though it sat at the perfect height For Captain Brooks to fuck someone. She shuddered at the image of herself bound to the horse and being fucked, just like her tormentor had suggested. A large padded wheel with cuffs for wrists and ankles dominated another wall. And last but certainly not least, Kim’s gaze fell on a large bed that looked like a half oval. It had neatly made red and black shinny sheets and she could tell just by looking at them that they were made of latex. The headboard was a long metal arch with hoops attached to it; more of which were situated on the base.

 _She’s got an entire bondage dungeon in her prison!_ The sight of the room filled Kim with terror and she suddenly became much more aware of her new nipple rings. She did not want to know how many of the rooms various pieces of bondage gear, toys and furniture she’d be forced to endure before she could escape. Feeling completely drained, she slowly lowered herself back down to the rabbit fur rug and closed her eyes. This was going to be a long ordeal and she could only hope she could find the strength to endure it. Otherwise, her new mistress might just manage to permanently break her. 

##

Kim sat bolt upright, sweat pouring down her body and gasped for air. Her bedsheets had tangled themselves around her and she frantically struggled to free herself. _Letmego, letmego, letmego!_ Throwing the blankets aside, her hands shot up her lilac pyjama top and to her nipples; both unadorned and unpierced. _A nightmare… just a nightmare._ Every single fibre of her being ached and though she now knew it had not been real, Kim felt a lasting echo of the pain from each and every lash she’d taken to her back and ass, the deep throb inside her aching vagina from the sheer intensity of the fucking she’d received and the sharp hot pain from the clamps on her breasts and the needle that had just recently pierced her nipples.

Breaths coming in ragged pants, she shifted her legs slightly and froze. Tentatively, scared of what she knew she would find, Kim slipped a hand inside her trousers and touched in between her legs; she was absolutely soaking. “Oh, God,” she uttered in the echo of a ghostly whisper. As abhorrent as it may have been, she knew what had happened. Her mind had played out that horrible scenario while she slept and her body had reacted. And she could tell from the sheer wetness, that she had both enjoyed it and most likely orgasmed. All alone and at the mercy of a perverted mind that seemed to revel in tormenting her, Kim broke down into an uncontrollable flood of tears. Maybe it was time she talked to Shego.

**Author's Note:**

> Hey, everyone. Thank you so much for taking the time to read this story. I hope you all enjoyed it. I would love to hear all your thoughts on it. If you enjoyed it, please consider reading And You And I; the work from which it originated. The link is provided below. If I feel inspired, I might write a sequel to this story. 
> 
> https://archiveofourown.org/works/23734132/chapters/56996365
> 
> Thanks once again and I hope you enjoyed it.
> 
> Warmest regards  
> Niaxi


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